Macclesfield progressed through four qualifying rounds to make their first appearance in the FA Cup first round in 1960, but lost 7-2 to Southport. The following season the club won the Cheshire League, beginning an eight year period in which they won three league titles and finished no lower than fifth, and in 1964 won the Cheshire League by a record equalling thirteen point margin. The club reached the FA Cup third round for the first time in 1968, meeting First Division Fulham at Craven Cottage. Macclesfield lost 4-2, but the performance resulted in Macclesfield's Keith Goalen becoming the first ever non-league player to be named Footballer of the Month by the London Evening Standard.
The club were founder members of the Northern Premier League, one of three leagues at the fifth tier of English football, upon its creation in 1968. Macclesfield were champions in each of the first two seasons of the competition, finishing twelve points clear in 1968-69, and by goal average in 1969-70. The 1969-70 season also resulted in a trip to Wembley for the inaugural final of the FA Trophy, a knockout competition for non-league clubs. Macclesfield defeated Telford United 2-0 in front of more than 28,000 spectators to win the competition. A period of decline then followed, despite heroic performances by the great Willie Mailey in goal, and the side's fortunes reached a nadir when the club finished bottom of the Northern Premier League in 1979, a year when the stronger teams from the division formed the national Alliance Premier League (now known as the Conference). The 1980s saw steady rebuilding. The club finished as Northern Premier League runners-up in the 1984-85 season, and two years later Macclesfield's third Northern Premier League title resulted in promotion to the Conference.
Macclesfield finished in mid-table in their first Conference season, and eliminated two League teams, Carlisle and Rotherham from the FA Cup. The club reached the FA Trophy final for the second time in 1989, facing Telford United, the same opponents as Macclesfield's first final nineteen years earlier. However, the team did not match the achievement of their predecessors, losing 1-0. From a high of a fourth place league finish in 1989-90, Macclesfield's final standing diminished each season, and following a struggle against relegation in 1992-93, manager Peter Wragg was sacked, and replaced with former Manchester United midfielder Sammy McIlroy.
Upon gaining League status, the club turned fully professional. Macclesfield's first League match was a 2-1 win at home to Torquay United. The momentum of the Conference success continued, and in their first League season, Macclesfield finished runners-up in Division Three and were promoted for the second consecutive season, this time to Division Two. It was a memorable year for the club, who were unbeaten at home for the entire season. However, the higher level proved a step too far for the club, who finished the 1998-99 season bottom of Division Two and were relegated. McIlroy soon left to become the Northern Ireland national coach and over the next five seasons a succession of managers including Gil Prescott, David Moss and club stalwart John Askey all took charge of the club without reaching the heights of the McIlroy era.
However, 2005/06 proved disappointing with the team failing to build on the previous season's progress, finishing an undistinguished 17th. Horton was sacked by the club in late September 2006, following a dismal start to the season in which Horton failed to secure a win in the twelve games prior to his dismissal, leaving the club bottom of the Football League. On October 23 2006, former Manchester United, Inter and England player Paul Ince was confirmed as Macclesfield's new player-manager. He lost his first match in charge 3-2 to Mansfield Town, and it took Macclesfield until twenty games into the season to record their first league win under Ince on December 5 2006. The team then went on a nine match unbeaten run, which earned a cup tie against champions Chelsea F.C. away in the 3rd round of the FA Cup, though, despite their fantastic away support and performance on the day, lost 6-1. Most of this was attributed to the decision to send off Macclesfield goalkeeper Tommy Lee, which replays have shown since to be inconclusive to merit a red card, with many believing that, in the spirit of the FA Cup, a red card was unwarranted.
They were then just able to survive after drawing 1-1 with Notts County on the final day of the 2006/07 season, after a poor run of results landed the team back in the relegation zone.
On 29th June 2007 Ian Brightwell was announced as their new manager with Asa Hartford as his assistant for the 2007/08 season as a replacement for former boss Paul Ince who left to become MK Dons manager earlier in the month. Macclesfield started the 2007-08 season away with a 1-1 draw to former Premier League club Bradford City and narrowly lost 1-0 to another former Premier League team Leeds United in the first round of the League Cup. In January, Chairman Rob Bickerton left the club after 7 years of services to join Shrewsbury and was replaced with Club Supporter Mike Rance and ex-player Andy Scott, founder of Bank Fashion Retail stores as Vice-Chairman.
On 27th February 2008 Keith Alexander was named manager, replacing Ian Brightwell who left the club immediately with his assistant Asa Hartford. The change was due to a poor run of results, which left the club 1 place and two points above the relegation places.
They have started the 2008-09 season in disappointing form in which they have not scored a single league goal in there opening four games. They have done rather well in the league cup in which they landed a money spinning tie against West Ham United after successfully beating Coca-Cola Championship side Blackpool 2-1 in the first round. They lost this match 4-1 in extra time.
Saga of the Silkmen (p. 85) and the News of the World Football Annual both give the record attendance of Moss Rose games involving Macc. Town as 9,003, in the Cheshire Cup tie vs. Winsford United, 14th Feb 1948, but this was an away match.
Since the building of the McAlpine Stand, a number of projects to improve the ground have been put forward including a new 'Silkman End' with Fitness Facilities and capacity for 2,500 fans. These plans were dropped due to lack of financial backing. A smaller project to incorporate a roof onto the stand was proposed but no plans have been firmly set.
In September 2007, the Club released a statement for the possibility of relocating to a new Stadium, approximately 1 mile south from the Moss Rose to the proposed South Macclesfield Development Area'.
The club crest is based upon the coat of arms of Macclesfield, and features a blue Lion Rampant holding a wheatsheaf.
A new club crest was planned for the start of the 2007-08 season. However, many loyal supporters were not happy with the modern design so the plans were delayed and a re-designed badge was introduced in early 2008, which has won the appraisal of the majority of fans.
Macclesfield's traditional rivals are Altrincham, a rivalry dating back to when both clubs were in the Cheshire League, and later the Northern Premier League and Conference. As far back as 1911 the Macclesfield and Altrincham teams were engaged in a close tussle for the Manchester League title - won narrowly by the Silkmen. However, the clubs have not shared the same division since 1996.
Famous fans include Stephen Morris of the band New Order, actor Marshall Lancaster and also FiveLive commentator Alan Green. The Rock is also a Macclesfield Town fan after choosing it out of a hat on Soccer AM.
John Askey holds the overall appearance record for the club in all competitions. His 20 year playing career taking in more than 700 games. John remains at the club and has also managed the Reserves to a League title and currently manages the Youth Team. John was manager of the first team for six months before the arrival of Brian Horton. Steve Wood played for Macclesfield and became a real hero for them during his time played at Macclesfield Town F.C
The most goals scored by a Macclesfield player in a single season is 83, achieved by Albert Valentine in the 1933-34 season.